Leonardtown Maryland Homes for Sale

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39725 Lady Baltimore Avenue Leonardtown, MD MLS# MDSM2029556 - Image 1

39725 Lady Baltimore Avenue Leonardtown, MD MLS# MDSM2029556 - Image 2

39725 Lady Baltimore Avenue Leonardtown, MD MLS# MDSM2029556 - Image 3

1 of 3

$335,000

Beds

2.0

Baths

1,886

Sq.Ft.

39725 Lady Baltimore Avenue

Leonardtown, MD

Courtesy of CENTURY 21 NEW MILLENNIUM

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 1

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 2

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 3

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 4

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 5

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 6

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 7

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 8

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 9

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 10

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 11

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 12

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 13

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 14

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 15

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 16

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 17

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 18

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 19

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 20

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 21

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 22

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 23

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 24

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 25

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 26

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 27

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 28

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 29

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 30

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 31

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 32

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 33

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 34

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 35

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 36

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 37

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 38

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 39

22343 Newtowne Neck Road Leonardtown, MD MLS# MDSM2029528 - Image 40

1 of 40

$474,900

Beds

2.0

Baths

2,114

Sq.Ft.

22343 Newtowne Neck Road

Leonardtown, MD

Courtesy of CENTURY 21 NEW MILLENNIUM

22204 Nomoni Street Leonardtown, MD MLS# MDSM2029298 - Image 1

22204 Nomoni Street Leonardtown, MD MLS# MDSM2029298 - Image 2

22204 Nomoni Street Leonardtown, MD MLS# MDSM2029298 - Image 3

22204 Nomoni Street Leonardtown, MD MLS# MDSM2029298 - Image 4

22204 Nomoni Street Leonardtown, MD MLS# MDSM2029298 - Image 5

22204 Nomoni Street Leonardtown, MD MLS# MDSM2029298 - Image 6

22204 Nomoni Street Leonardtown, MD MLS# MDSM2029298 - Image 7

22204 Nomoni Street Leonardtown, MD MLS# MDSM2029298 - Image 8

22204 Nomoni Street Leonardtown, MD MLS# MDSM2029298 - Image 9

22204 Nomoni Street Leonardtown, MD MLS# MDSM2029298 - Image 10

22204 Nomoni Street Leonardtown, MD MLS# MDSM2029298 - Image 11

22204 Nomoni Street Leonardtown, MD MLS# MDSM2029298 - Image 12

22204 Nomoni Street Leonardtown, MD MLS# MDSM2029298 - Image 13

22204 Nomoni Street Leonardtown, MD MLS# MDSM2029298 - Image 14

22204 Nomoni Street Leonardtown, MD MLS# MDSM2029298 - Image 15

22204 Nomoni Street Leonardtown, MD MLS# MDSM2029298 - Image 16

22204 Nomoni Street Leonardtown, MD MLS# MDSM2029298 - Image 17

22204 Nomoni Street Leonardtown, MD MLS# MDSM2029298 - Image 18

22204 Nomoni Street Leonardtown, MD MLS# MDSM2029298 - Image 19

22204 Nomoni Street Leonardtown, MD MLS# MDSM2029298 - Image 20

22204 Nomoni Street Leonardtown, MD MLS# MDSM2029298 - Image 21

22204 Nomoni Street Leonardtown, MD MLS# MDSM2029298 - Image 22

22204 Nomoni Street Leonardtown, MD MLS# MDSM2029298 - Image 23

22204 Nomoni Street Leonardtown, MD MLS# MDSM2029298 - Image 24

22204 Nomoni Street Leonardtown, MD MLS# MDSM2029298 - Image 25

22204 Nomoni Street Leonardtown, MD MLS# MDSM2029298 - Image 26

22204 Nomoni Street Leonardtown, MD MLS# MDSM2029298 - Image 27

22204 Nomoni Street Leonardtown, MD MLS# MDSM2029298 - Image 28

22204 Nomoni Street Leonardtown, MD MLS# MDSM2029298 - Image 29

22204 Nomoni Street Leonardtown, MD MLS# MDSM2029298 - Image 30

22204 Nomoni Street Leonardtown, MD MLS# MDSM2029298 - Image 31

22204 Nomoni Street Leonardtown, MD MLS# MDSM2029298 - Image 32

22204 Nomoni Street Leonardtown, MD MLS# MDSM2029298 - Image 33

22204 Nomoni Street Leonardtown, MD MLS# MDSM2029298 - Image 34

Virtual Tour

1 of 34

$315,000

Beds

2.0

Baths

1,008

Sq.Ft.

22204 Nomoni Street

Leonardtown, MD

Courtesy of REDFIN CORP

THE TIME TO SELL IS NOW!

Lot 113 - 23696 Weeping Willow Way Leonardtown, MD MLS# MDSM2029482 - Image 1

Lot 113 - 23696 Weeping Willow Way Leonardtown, MD MLS# MDSM2029482 - Image 2

Lot 113 - 23696 Weeping Willow Way Leonardtown, MD MLS# MDSM2029482 - Image 3

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Lot 113 - 23696 Weeping Willow Way Leonardtown, MD MLS# MDSM2029482 - Image 38

Lot 113 - 23696 Weeping Willow Way Leonardtown, MD MLS# MDSM2029482 - Image 39

Lot 113 - 23696 Weeping Willow Way Leonardtown, MD MLS# MDSM2029482 - Image 40

Lot 113 - 23696 Weeping Willow Way Leonardtown, MD MLS# MDSM2029482 - Image 41

Lot 113 - 23696 Weeping Willow Way Leonardtown, MD MLS# MDSM2029482 - Image 42

New Construction with Virtual Tour

1 of 42

$479,900

Beds

3.1

Baths

Lot 113 - 23696 Weeping Willow Way

Leonardtown, MD

Courtesy of RE/MAX ONE

Lot 133 - 23691 Weeping Willow Way Leonardtown, MD MLS# MDSM2029484 - Image 1

Lot 133 - 23691 Weeping Willow Way Leonardtown, MD MLS# MDSM2029484 - Image 2

Lot 133 - 23691 Weeping Willow Way Leonardtown, MD MLS# MDSM2029484 - Image 3

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Lot 133 - 23691 Weeping Willow Way Leonardtown, MD MLS# MDSM2029484 - Image 7

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Lot 133 - 23691 Weeping Willow Way Leonardtown, MD MLS# MDSM2029484 - Image 11

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Lot 133 - 23691 Weeping Willow Way Leonardtown, MD MLS# MDSM2029484 - Image 36

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Lot 133 - 23691 Weeping Willow Way Leonardtown, MD MLS# MDSM2029484 - Image 38

Lot 133 - 23691 Weeping Willow Way Leonardtown, MD MLS# MDSM2029484 - Image 39

Lot 133 - 23691 Weeping Willow Way Leonardtown, MD MLS# MDSM2029484 - Image 40

New Construction with Virtual Tour

1 of 40

$489,900

Beds

3.1

Baths

Lot 133 - 23691 Weeping Willow Way

Leonardtown, MD

Courtesy of RE/MAX ONE

Lot 101 - 23713 Dragonfly Lane Leonardtown, MD MLS# MDSM2029486 - Image 1

Lot 101 - 23713 Dragonfly Lane Leonardtown, MD MLS# MDSM2029486 - Image 2

Lot 101 - 23713 Dragonfly Lane Leonardtown, MD MLS# MDSM2029486 - Image 3

Lot 101 - 23713 Dragonfly Lane Leonardtown, MD MLS# MDSM2029486 - Image 4

Lot 101 - 23713 Dragonfly Lane Leonardtown, MD MLS# MDSM2029486 - Image 5

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Lot 101 - 23713 Dragonfly Lane Leonardtown, MD MLS# MDSM2029486 - Image 7

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Lot 101 - 23713 Dragonfly Lane Leonardtown, MD MLS# MDSM2029486 - Image 33

Lot 101 - 23713 Dragonfly Lane Leonardtown, MD MLS# MDSM2029486 - Image 34

New Construction with Virtual Tour

1 of 34

OPEN HOUSE: Saturday 3/21 3:00 PM - 5:00 PM

$449,900

Beds

3.1

Baths

Lot 101 - 23713 Dragonfly Lane

Leonardtown, MD

Courtesy of RE/MAX ONE

Lot 99 - 23725 Dragonfly Lane Leonardtown, MD MLS# MDSM2029488 - Image 1

Lot 99 - 23725 Dragonfly Lane Leonardtown, MD MLS# MDSM2029488 - Image 2

Lot 99 - 23725 Dragonfly Lane Leonardtown, MD MLS# MDSM2029488 - Image 3

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Lot 99 - 23725 Dragonfly Lane Leonardtown, MD MLS# MDSM2029488 - Image 35

New Construction with Virtual Tour

1 of 35

OPEN HOUSE: Saturday 3/21 3:00 PM - 5:00 PM

$449,900

Beds

3.1

Baths

Lot 99 - 23725 Dragonfly Lane

Leonardtown, MD

Courtesy of RE/MAX ONE

44545 Brewer Lane Leonardtown, MD MLS# MDSM2029400 - Image 1

44545 Brewer Lane Leonardtown, MD MLS# MDSM2029400 - Image 2

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1 of 69

$674,900

Beds

3.1

Baths

3,243

Sq.Ft.

44545 Brewer Lane

Leonardtown, MD

Courtesy of CENTURY 21 NEW MILLENNIUM

41516 Marwood Circle Leonardtown, MD MLS# MDSM2029470 - Image 1

41516 Marwood Circle Leonardtown, MD MLS# MDSM2029470 - Image 2

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41516 Marwood Circle Leonardtown, MD MLS# MDSM2029470 - Image 7

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1 of 55

OPEN HOUSE: Saturday 3/21 1:00 PM - 3:00 PM

$437,000

Beds

3.1

Baths

2,402

Sq.Ft.

41516 Marwood Circle

Leonardtown, MD

Courtesy of CENTURY 21 NEW MILLENNIUM

41438 Silver Charm Court Leonardtown, MD MLS# MDSM2029268 - Image 1

41438 Silver Charm Court Leonardtown, MD MLS# MDSM2029268 - Image 2

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1 of 105

$690,000

Beds

3.1

Baths

4,180

Sq.Ft.

41438 Silver Charm Court

Leonardtown, MD

Courtesy of RE/MAX ONE

Lot 100 - 23719 Dragonfly Lane Leonardtown, MD MLS# MDSM2029208 - Image 1

Lot 100 - 23719 Dragonfly Lane Leonardtown, MD MLS# MDSM2029208 - Image 2

Lot 100 - 23719 Dragonfly Lane Leonardtown, MD MLS# MDSM2029208 - Image 3

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Lot 100 - 23719 Dragonfly Lane Leonardtown, MD MLS# MDSM2029208 - Image 44

Lot 100 - 23719 Dragonfly Lane Leonardtown, MD MLS# MDSM2029208 - Image 45

New Construction

1 of 45

$449,900

Beds

3.1

Baths

2,571

Sq.Ft.

Lot 100 - 23719 Dragonfly Lane

Leonardtown, MD

Courtesy of RE/MAX ONE

Lot 117 - 23720 Weeping Willow Way Leonardtown, MD MLS# MDSM2029218 - Image 1

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Lot 117 - 23720 Weeping Willow Way Leonardtown, MD MLS# MDSM2029218 - Image 45

Lot 117 - 23720 Weeping Willow Way Leonardtown, MD MLS# MDSM2029218 - Image 46

New Construction with Virtual Tour

1 of 46

$489,900

Beds

3.1

Baths

3,095

Sq.Ft.

Lot 117 - 23720 Weeping Willow Way

Leonardtown, MD

Courtesy of RE/MAX ONE

Lot 112 - 23690 Weeping Willow Way Leonardtown, MD MLS# MDSM2029220 - Image 1

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Lot 112 - 23690 Weeping Willow Way Leonardtown, MD MLS# MDSM2029220 - Image 45

Lot 112 - 23690 Weeping Willow Way Leonardtown, MD MLS# MDSM2029220 - Image 46

New Construction with Virtual Tour

1 of 46

$489,900

Beds

3.1

Baths

3,095

Sq.Ft.

Lot 112 - 23690 Weeping Willow Way

Leonardtown, MD

Courtesy of RE/MAX ONE

Lot 102 - 23707 Dragonfly Lane Leonardtown, MD MLS# MDSM2029202 - Image 1

Lot 102 - 23707 Dragonfly Lane Leonardtown, MD MLS# MDSM2029202 - Image 2

Lot 102 - 23707 Dragonfly Lane Leonardtown, MD MLS# MDSM2029202 - Image 3

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Lot 102 - 23707 Dragonfly Lane Leonardtown, MD MLS# MDSM2029202 - Image 21

Lot 102 - 23707 Dragonfly Lane Leonardtown, MD MLS# MDSM2029202 - Image 22

Lot 102 - 23707 Dragonfly Lane Leonardtown, MD MLS# MDSM2029202 - Image 23

Lot 102 - 23707 Dragonfly Lane Leonardtown, MD MLS# MDSM2029202 - Image 24

Lot 102 - 23707 Dragonfly Lane Leonardtown, MD MLS# MDSM2029202 - Image 25

Lot 102 - 23707 Dragonfly Lane Leonardtown, MD MLS# MDSM2029202 - Image 26

Lot 102 - 23707 Dragonfly Lane Leonardtown, MD MLS# MDSM2029202 - Image 27

Lot 102 - 23707 Dragonfly Lane Leonardtown, MD MLS# MDSM2029202 - Image 28

Lot 102 - 23707 Dragonfly Lane Leonardtown, MD MLS# MDSM2029202 - Image 29

Lot 102 - 23707 Dragonfly Lane Leonardtown, MD MLS# MDSM2029202 - Image 30

New Construction

1 of 30

$479,900

Beds

3.1

Baths

Lot 102 - 23707 Dragonfly Lane

Leonardtown, MD

Courtesy of RE/MAX ONE

22547 Landing Way Leonardtown, MD MLS# MDSM2029148 - Image 1

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1 of 48

OPEN HOUSE: Saturday 3/21 11:00 AM - 1:00 PM

$515,000

Beds

3.1

Baths

2,764

Sq.Ft.

22547 Landing Way

Leonardtown, MD

Courtesy of EXP REALTY, LLC

43641 Redmond Road Leonardtown, MD MLS# MDSM2029078 - Image 1

43641 Redmond Road Leonardtown, MD MLS# MDSM2029078 - Image 2

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43641 Redmond Road Leonardtown, MD MLS# MDSM2029078 - Image 17

43641 Redmond Road Leonardtown, MD MLS# MDSM2029078 - Image 18

1 of 18

$589,000

Studio

Beds

0.0

Baths

2,184

Sq.Ft.

43641 Redmond Road

Leonardtown, MD

Courtesy of RE/MAX ONE

St. Andrews Church Road Leonardtown, MD MLS# MDSM2029070 - Image 1

St. Andrews Church Road Leonardtown, MD MLS# MDSM2029070 - Image 2

St. Andrews Church Road Leonardtown, MD MLS# MDSM2029070 - Image 3

St. Andrews Church Road Leonardtown, MD MLS# MDSM2029070 - Image 4

St. Andrews Church Road Leonardtown, MD MLS# MDSM2029070 - Image 5

St. Andrews Church Road Leonardtown, MD MLS# MDSM2029070 - Image 6

1 of 6

$175,000

Studio

Beds

0.0

Baths

St. Andrews Church Road

Leonardtown, MD

Courtesy of BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY

22393 Saint Clements Avenue Leonardtown, MD MLS# MDSM2029036 - Image 1

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Virtual Tour

1 of 68

$778,900

Beds

2.2

Baths

2,097

Sq.Ft.

22393 Saint Clements Avenue

Leonardtown, MD

Courtesy of LISTWITHFREEDOM.COM

23369 Marview Court Leonardtown, MD MLS# MDSM2028828 - Image 1

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1 of 58

$435,000

Beds

3.1

Baths

2,308

Sq.Ft.

23369 Marview Court

Leonardtown, MD

Courtesy of CENTURY 21 NEW MILLENNIUM

40736 Center 40 Circle Leonardtown, MD MLS# MDSM2028808 - Image 1

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1 of 58

$415,000

Beds

2.1

Baths

1,829

Sq.Ft.

40736 Center 40 Circle

Leonardtown, MD

Courtesy of CENTURY 21 NEW MILLENNIUM

About Leonardtown

Listings in Leonardtown, MD: 71
Estimated median home price: $515,000

Leonardtown MD Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Leonardtown, Maryland real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Leonardtown, MD.

Homes for Sale by Price in Leonardtown, MD

Price	Count
$0 - 100K	1
$100K - 200K	8
$200K - 300K	1
$300K - 400K	3
$400K - 500K	22
$500K - 600K	11
$600K - 700K	13
$700K - 800K	5
$800K - 900K	1
$900K - 1M	0
$1M - Max	6

Homes for Sale by Type in Leonardtown, MD

Property Type	Count
Single Family	42
Townhouse	16
Condo	1
Commercial	1
Rental	19
Lots and Land	11
Condo/Town/CoOp	0
CoOp	0
Multi Family	0
Mobile Home	0
Farms	0

(Data as of 3/18/2026)

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20650

Information deemed reliable but not guaranteed.

Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BrightMLS Broker Reciprocity^SM program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Weichert, Realtors® participates, and is provided by BrightMLS through a licensing agreement.

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Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale.

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Leonardtown Maryland Homes for Sale

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